Alkylated hydroxy-substituted aromatic compounds are useful in the chemical industry for a variety of purposes. For example, t-butylhydroquinone has been shown to possess excellent anti-oxidant properties with a concomitant low toxicity. Therefore, it is possible to utilize this compound as an anti-oxidant in the food industry being especially useful as an anti-oxidant for fats, lards, oils and fat-containing foods, either by incorporation into the food stuff itself or by being incorporated in the material which is used to encase or wrap the particular food stuff. Likewise, t-butylphenol will find a use as a plasticizer, as an intermediate for anti-oxidants, as a pore-point depressor, an emulsion breaker for petroleum oils and some plastics, as an intermediate for synthetic resins, surface active agents, perfumes, etc.
Di-t-butylphenol and di-t-butylhydroquinone have also found many uses as anti-oxidants. 2,6-di-t-butylphenol is an anti-oxidant for gasoline and 4-methyl-2,6-di-t-butylphenol is an anti-oxidant in the food industry and in rubbers, paints and plastics. 2,5-di-t-butylhydroquinone is a polymer inhibitor and an anti-oxidant in vegetable fats and oils as well as a stabilizer against the ultraviolet deterioration of rubber.
One method for effecting the alkylation of these compounds is to alkylate a hydroxy-substituted aromatic compound like hydroquinone with an alkylating agent in the presence of an acidic catalyst and in a reaction medium comprising a hydrocarbon solvent. However, the amount of the di-alkylated product is usually low.
As will hereinafter be shown in greater detail, it has now been discovered that by effecting the alkylation reaction in the presence of a certain catalytic composition of matter, it is possible to obtain a higher degree or greater yield of di-alkylated product. In addition, it is also possible by utilizing this catalyst to effect the reaction at a relatively low temperature, thereby decreasing the amount of energy required with a greater savings of cost.